5100
K. Bahrami et al. / Tetrahedron 68 (2012) 5095e5101
extracts were dried with MgSO4 and concentrated under reduced
pressure to give the corresponding sulfonamide product in excel-
lent yield.
cyclohexyl),1.91e1.96 (2H, m, CH2 of cyclohexyl), 2.30e2.34 (2H, m,
CH2 of cyclohexyl), 2.35 (3H, s, CH3), 3.11e3.23 (1H, m, CH of
cyclohexyl), 7.10e7.21 (4H, m, Ph). 13C NMR (50 MHz, CDCl3):
dC¼20.4, 25.5, 24.6, 26.1, 59.5, 121.3, 129.9, 136.4, 146.4.
4.3. General procedure for the synthesis of sulfonic ester
4.3.6. Dip-tolyl propane-1,3-disulfonate (5l). Yellow oil. Found: C,
53.18; H, 5.11; S, 16.34. C17H20S2O6 requires C, 53.11; H, 5.24; S,
16.68. Rf¼0.37 (8:3 n-hexane/EtOAc); IR (liquid film, cmꢀ1) 3035,
2929, 1502, 1462, 1361, 1173, 1146; 1H NMR (200 MHz, CDCl3):
dH¼2.41 (6H, s, 2CH3), 2.62e2.69 (2H, m, eCH2eCH2eCH2e), 3.53
(4H, t, J¼7.2 Hz, -SO2-CH2-), 7.18e7.28 (8H, m, 2Ph). 13C NMR
(50 MHz, CDCl3): dC¼18.6, 20.9, 47.9, 121.7, 130.6, 137.5, 146.7.
A mixture of thiol (1 mmol), H2O2 (30%, 3 mmol, 0.3 mL), and
POCl3 (1 mmol, 0.153 g) was stirred in CH3CN (5 mL) at 25 ꢁC for the
appropriate period of time. When TLC showed complete con-
sumption of the thiol, a solution of phenol derivative (1 mmol) and
Amberlite IRA-400 (OHꢀ) (0.1 g, containing 0.1 mmol of OHꢀ) in
CH3CN (2 mL) was added. The resulting mixture was stirred at room
temperature until TLC showed the disappearance of all the starting
material. The catalyst was filtered off and the filtrate was concen-
trated in vacuo. The reaction mixture was then diluted with water
(10 mL) and extracted with EtOAc (3ꢂ10 mL). The combined ethyl
acetate extracts were dried with MgSO4 and concentrated under
reduced pressure to give the corresponding sulfonic ester as only
product. In all the cases, the product obtained after the usual work
up gave satisfactory spectral data. Spectral and analytical data for
new compounds follow.
Acknowledgements
We are thankful to the Razi University Research Council for
partial support of this work.
Supplementary data
Supplementary data associated with this article can be found in
4.3.1. N1,N3-Dicyclohexylpropane-1,3-disulfonamide (3h). Light beige
oil. Found: C, 48.90; H, 8.21; N, 7.40 S,17.48. C15H30N2S2O4 requires C,
49.15; H, 8.25; N, 7.64 S, 17.50. Rf¼0.78 (8:3 n-hexane/EtOAc); IR
(liquid film, cmꢀ1) 3294, 2931, 2856, 1724, 1452, 1309, 1128; 1H NMR
(200 MHz, CDCl3): dH¼0.85e1.52 (12H, m, CH2 cyclohexyl),1.62e2.27
(8H, m, CH2 of cyclohexyl), 2.31e2.51 (2H, m, eCH2eCH2eSO2e),
2.81e2.93 (2H, m, CH cyclohexyl), 3.11e3.51 (4H, m, CH2eSO2e), 6.08
(2H, br, NH). 13C NMR (50 MHz, CDCl3): dC¼24.3, 24.8, 25.1, 34.5, 51.8,
52.9.
References and notes
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4.3.2. 3-(N-p-Tolylsulfamoyl)propane-1-sulfonyl chloride (3i). Orange
oil. Found: C, 38.35; H, 4.55; N, 4.28; S, 20.34. C10H14NS2O4Cl requires
C, 38.52; H, 4.53; N, 4.49; S, 20.57. Rf¼0.73 (8:3 n-hexane/EtOAc); IR
(liquid film, cmꢀ1) 3290, 2929, 2860, 1724, 1453, 1306, 1167, 1128; 1H
NMR (200 MHz, CDCl3): dH¼2.37 (3H, s, CH3), 2.64e2.71 (2H, m,
CH2eCH2eCH2), 3.49 (2H, t, J¼6.7 Hz, eCH2eSO2eNHe), 3.78 (2H, t,
J¼6.7 Hz, eCH2eSO2Cl), 4.27 (1H, br, NH), 7.17e7.19 (4H, m, Ph). 13
C
NMR (50 MHz, CDCl3): dC¼21.0, 24.6, 36.4, 57.9, 121.2, 129.8, 133.4,
135.1.
4.3.3. Phenyl naphthalene-2-sulfonate (5c). Cream solid: mp¼
91e92 ꢁC. Found: C, 67.47; H, 4.15; S, 11.12. C16H12SO3 requires C,
67.59; H, 4.25; S, 11.28. Rf¼0.58 (8:3 n-hexane/EtOAc); IR (KBr,
cmꢀ1) 3059, 2920, 1502, 1375, 1460, 1375, 1176, 1149; 1H NMR
(200 MHz, CDCl3): dH¼6.98e7.03 (2H, m, o-H of Ph), 7.23e7.28 (3H,
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m, Ph), 7.70e7.98 (6H, m, naphthyl), 8.38 (1H, s, a-H of naphthyl).
13C NMR (50 MHz, CDCl3): dC¼122.0 122.5, 126.8, 127.4, 127.8, 129.0
129.1, 129.2, 129.3, 130.0, 131.3, 131.3, 136.0, 149.6.
4.3.4. Naphthalen-2-yl phenylmethanesulfonate (5i). Light pink
solid: mp¼73e75 ꢁC. Found: C, 68.21; H, 4.50; S, 10.65. C17H14SO3
requires C, 68.44; H, 4.73; S, 10.75. Rf¼0.55 (8:3 n-hexane/EtOAc);
IR (KBr, cmꢀ1) 3055, 2995, 2949, 1463, 1360, 1213, 1173, 1146; 1H
NMR (200 MHz, CDCl3): dH¼4.61 (2H, s, eCH2ePh), 7.26e7.31 (1H,
m, H-3 of naphthyl), 7.46e7.64 (8H, m, 5CH of Ph, 3CH of naphthyl),
7.81e7.90 (3H, m, 3H of naphthyl). 13C NMR (50 MHz, CDCl3):
dC¼56.4, 119.0, 120.5, 126.1, 126.6, 126.8, 127.4, 127.5, 128.6, 128.9,
129.7, 130.5, 131.5, 133.1, 146.4.
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4.3.5. p-Tolyl cyclohexanesulfonate (5j). Brown oil. Found: C, 61.15;
H, 7.23; S, 12.43. C13H18SO3 requires C, 61.39; H, 7.13; S, 12.61.
Rf¼0.64 (8:3 n-hexane/EtOAc); IR (Liquid film, cmꢀ1) 3062, 2941,
2862, 1616, 1514, 1464, 1354, 1194, 1144; 1H NMR (200 MHz, CDCl3):
dH¼1.26e1.37 (3H, m, CH2 of cyclohexyl), 1.55e1.82 (3H, m, CH2 of
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